Pyridine → 6-bromo-1-(3-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-2-(hydroxymethyl)phenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

Participants

Reaction Conditions

Reaction Steps

In a 25 mL round-bottomed flask, 6-bromo-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile (75.0 mg, 338 μmol, Eq: 1.19), 6-tert-butyl-8-fluoro-2-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-4-yl)phthalazin-1(2H)-one (100 mg, 284 μmol, Eq: 1.00) and copper acetate (52.2 mg) were combined with 1,2-dichloroethane (3.00 ml) to give a blue suspension. Pyridine (44.9 mg, 45.9 μl, 568 μmol, Eq: 2) was added. The reaction mixture was heated to 45° C. and stirred for 2 d. Mixture was poured into 20 mL sat NH4Cl and extracted with EtOAc (3×20 mL). The organic layers were dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 40 g, 25% to 45% EtOAc in hexanes) to give 6-bromo-1-(3-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-2-(hydroxymethyl)phenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile (16 mg, 10.3%).

Provenance & Evidence